(1R,3aS,7aS)-1-hydroxy-5,7,7-trimethyl-1,3,3a,7a-tetrahydro-2-benzofuran-4-one

Details

• Internal ID: 9697a4a1-7ad6-41cd-9ba1-9847730b7151
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: (1R,3aS,7aS)-1-hydroxy-5,7,7-trimethyl-1,3,3a,7a-tetrahydro-2-benzofuran-4-one
• SMILES (Canonical): CC1=CC(C2C(C1=O)COC2O)(C)C
• SMILES (Isomeric): CC1=CC([C@@H]2[C@H](C1=O)CO[C@H]2O)(C)C
• InChI: InChI=1S/C11H16O3/c1-6-4-11(2,3)8-7(9(6)12)5-14-10(8)13/h4,7-8,10,13H,5H2,1-3H3/t7-,8-,10-/m1/s1
• InChI Key: GBYYWZSCZPZVLI-NQMVMOMDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₆O₃
• Molecular Weight: 196.24 g/mol
• Exact Mass: 196.109944368 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.12
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	-	0.6289	62.89%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7590	75.90%
OATP2B1 inhibitior	-	0.8510	85.10%
OATP1B1 inhibitior	+	0.9141	91.41%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.8512	85.12%
P-glycoprotein inhibitior	-	0.9104	91.04%
P-glycoprotein substrate	-	0.9224	92.24%
CYP3A4 substrate	+	0.5178	51.78%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	-	0.8704	87.04%
CYP3A4 inhibition	-	0.9056	90.56%
CYP2C9 inhibition	-	0.7178	71.78%
CYP2C19 inhibition	-	0.7276	72.76%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	-	0.9577	95.77%
CYP inhibitory promiscuity	-	0.6368	63.68%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4946	49.46%
Eye corrosion	-	0.9642	96.42%
Eye irritation	-	0.7063	70.63%
Skin irritation	-	0.5816	58.16%
Skin corrosion	-	0.9064	90.64%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8086	80.86%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.5966	59.66%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.4623	46.23%
Acute Oral Toxicity (c)	III	0.5498	54.98%
Estrogen receptor binding	-	0.6133	61.33%
Androgen receptor binding	-	0.5178	51.78%
Thyroid receptor binding	-	0.8010	80.10%
Glucocorticoid receptor binding	-	0.8344	83.44%
Aromatase binding	-	0.8887	88.87%
PPAR gamma	-	0.6385	63.85%
Honey bee toxicity	-	0.9275	92.75%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9284	92.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.50%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.15%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.04%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.38%	96.09%
CHEMBL1937	Q92769	Histone deacetylase 2	85.27%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.69%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.96%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.25%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.90%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.39%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.37%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.55%	85.14%

Plants that contains it

• Prangos uloptera

Cross-Links

• PubChem: 636977
• LOTUS: LTS0162984
• wikiData: Q105106288